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3-Bedroom Homes for Sale in Winter Park, FL with Private Pool

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  • /19

    $529,900

    • 3 Beds
    • 2 Baths
    • 2,254 Sq Ft

    7682 Glenmoor Ln, Winter Park, FL 32792

    Welcome to 7682 Glenmoor Lane – Located in the established community of Glenmoor, zoned for Winter Park HS, Maitland Middle and Lakemont Elementary.This beautifully renovated Winter Park gem is situated on a generous 0.26-acre lot, this stunning single-family home blends timeless style with modern updates throughout.Step inside to discover custom tile flooring, solid wood cabinetry in

    Bob Holston, Jr HOLSTON PROPERTIES & DEV., INC

    7682 Glenmoor Ln, Winter Park, FL 32792
  • /41

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft

    5331 Oak Ct, Winter Park, FL 32792

    Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

    Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

    5331 Oak Ct, Winter Park, FL 32792
  • /49

    $649,900

    • 3 Beds
    • 2 Baths
    • 1,469 Sq Ft

    1926 Natalen Rd, Winter Park, FL 32792

    *** MUST SEE WINTER PARK POOL HOME ***Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing

    Peggy Bonnewitz EXP REALTY LLC

    1926 Natalen Rd, Winter Park, FL 32792
  • /66

    $1,249,000

    • 3 Beds
    • 2.5 Baths
    • 1,993 Sq Ft

    2525 Venetian Way, Winter Park, FL 32789

    Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access This meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace. The sleek, chef-inspired kitchen

    Kimberly Slinger KELLY PRICE & COMPANY LLC

    2525 Venetian Way, Winter Park, FL 32789
  • /37

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft

    2758 Banchory Rd, Winter Park, FL 32792

    Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street,

    Erwin Vargas MR VARGAS PROPERTY MANAGEMENT LLC

    2758 Banchory Rd, Winter Park, FL 32792
  • /37

    $679,900

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft

    1640 Cypress Point Ln, Winter Park, FL 32792

    Welcome to 1640 Cypress Point – a home like no other in Winter Park. This beautifully maintained 3-bedroom, 2-bathroom home offers 1,704 sq. ft. overlooking a serene spring-fed pond and the Winter Park Pines Golf Course. Nestled on a quiet street with a cul-de-sac, this property combines privacy, natural beauty, and convenience in one exceptional location. As you walk up to the front door, you’ll

    Amy Turner KELLER WILLIAMS WINTER PARK

    1640 Cypress Point Ln, Winter Park, FL 32792
  • /39

    $699,900

    • 3 Beds
    • 3 Baths
    • 1,876 Sq Ft

    618 Blairshire Cir, Winter Park, FL 32792

    First time on the market! This one-owner, 3-bedroom, 3-bathroom single-family pool home offers the perfect blend of classic Florida charm and modern potential. Originally named The Polynesia, the home embraces open Florida living while offering distinct zones for privacy and comfort. A brand-new roof (2025) and 2 New HVAC 2024 provides peace of mind and a strong foundation for move-in readiness —

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    618 Blairshire Cir, Winter Park, FL 32792
  • /43

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,827 Sq Ft

    676 Dunblane Dr, Winter Park, FL 32792

    **ASSUMABLE VA LOAN at 2.25% Interest**Incredible opportunity to assume the seller’s VA mortgage at just 2.5% interest. 3 Beds | 2 Baths | Bonus Room | A meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community in Winter Park. This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full

    Emma Kaplan BALDWIN PARK REALTY LLC

    676 Dunblane Dr, Winter Park, FL 32792
  • /68

    $960,000

    • 3 Beds
    • 2 Baths
    • 2,114 Sq Ft

    250 Cortland Ave, Winter Park, FL 32789

    Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

    Alexandra Nordine EXP REALTY LLC

    250 Cortland Ave, Winter Park, FL 32789
  • /14

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft

    3383 Hamlet Loop, Winter Park, FL 32792

    Charming Winter Park Home with Private Pool on Corner Lot!Don’t miss this beautifully updated 3-bedroom, 2-bath single-family home nestled in a quiet, tucked-away neighborhood in the heart of Winter Park. Just minutes from the vibrant shops and restaurants of Park Avenue, this centrally located gem offers the perfect blend of comfort, convenience, and charm.Step inside to find

    Cliff Glansen FLATFEE.COM

    3383 Hamlet Loop, Winter Park, FL 32792
  • /74

    $1,750,000

    • 3 Beds
    • 4 Baths
    • 2,964 Sq Ft

    1270 Arlington Place, Winter Park, FL 32789

    Modern Elegance in the Heart of Winter Park!Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste.A long paver driveway welcomes

    Brian Mitnik RE/MAX 200 REALTY

    1270 Arlington Place, Winter Park, FL 32789
  • /27

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    4959 Ardmore Dr, Winter Park, FL 32792

    Tucked away at the end of a quiet cul-de-sac with no HOA, this home sits on an oversized lot that offers exceptional space, privacy, and flexibility. The layout features a desirable split floor plan, providing separation between the primary suite and guest bedrooms, perfect for families, guests, or a home office setup. This property was recently updated with new flooring throughout, a fully

    Brandon Geers COMPASS FLORIDA LLC

    4959 Ardmore Dr, Winter Park, FL 32792
  • /70

    $472,000 Open Sat 10AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,623 Sq Ft

    2648 Amsden Rd, Winter Park, FL 32792

    Beautiful Pool Home in Desirable Winter Park EstatesWelcome to this charming and thoughtfully updated pool home in the highly sought-after Winter Park Estates subdivision—zoned for top-rated schools, including Winter Park High School. This mid-century gem blends modern comfort with timeless style, located in one of Central Florida’s most beloved neighborhoods.Property

    Mary Dees CHOICEPOINTE REALTY, INC.

    2648 Amsden Rd, Winter Park, FL 32792
  • /50

    $489,000

    • 3 Beds
    • 3 Baths
    • 1,880 Sq Ft

    2835 Bongart Rd, Winter Park, FL 32792

    Motivated Seller - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard features fresh SOD, while the gables and

    Claudia Jenkins CHARLES RUTENBERG REALTY ORLANDO

    2835 Bongart Rd, Winter Park, FL 32792
  • /28

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,517 Sq Ft

    5547 Garden Grove Cir, Winter Park, FL 32792

    Winter Park, beautifully maintained 3-bedroom, 2-bathroom home nestled in the desirable Garden Grove neighborhood. Designed with an open floor plan and filled with natural light, this home offers versatile spaces perfect for both everyday living and entertaining.Step into the spacious Great Room which can be used for mulitple purposes like game room, home office or gym . The adjoining Kitchen

    Steve Dalton ROYALTY R E BOUTIQUE INC

    5547 Garden Grove Cir, Winter Park, FL 32792
  • /34

    $479,900

    • 3 Beds
    • 2 Baths
    • 1,939 Sq Ft

    3054 Bluebrook Dr, Winter Park, FL 32792

    Step into your dream home located in the charming Winter Park, Florida. This stunning property boasts 3 bedrooms and 2 bathrooms, perfect for a growing family or those who love to entertain.As you enter, you are greeted by a cozy fireplace, ideal for chilly Florida evenings. The spacious living room flows seamlessly into the gourmet kitchen, complete with granite countertops and stainless steel

    Trisha Deokinandan ALORA REALTY GROUP INC

    3054 Bluebrook Dr, Winter Park, FL 32792
  • /30

    $420,000

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    5001 Tangerine Ave, Winter Park, FL 32792

    Charming Winter Park Home with PoolWelcome to 5001 Tangerine Avenue, a bright and welcoming 3-bedroom, 2-bath home in the heart of Winter Park. Situated on a spacious 0.32-acre lot, this 1,732 sq ft home features an inviting layout perfect for relaxing or entertaining.Enjoy sunny Florida days by your private pool and take advantage of the large yard for outdoor fun or future

    Jason Neves MARK SPAIN REAL ESTATE

    5001 Tangerine Ave, Winter Park, FL 32792
  • /16

    $1,470,000

    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft

    1644 Hibiscus Ave, Winter Park, FL 32789

    Charming, Well-Maintained Home on a Prime Lot in Winter Park’s Coveted Tree StreetsDon’t miss this rare opportunity to own a beautifully landscaped and meticulously maintained property on one of the most desirable streets in Winter Park. Situated on one of the largest lots in the sought-after Tree Streets, this home is perfect for a buyer or builder ready to create something truly special

    Harry Pool, III COLDWELL BANKER RESIDENTIAL RE

    1644 Hibiscus Ave, Winter Park, FL 32789
  • /29

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    3214 Lowndes Dr, Winter Park, FL 32792

    Solar panels, 2019 roof, and 2019 AC! This beautifully remodeled 3-bedroom, 2-bathroom pool home offers 1,200 sq ft of updated living space in a quiet, friendly neighborhood. Inside, you'll find sleek modern finishes, an open-concept layout, and a kitchen with newer high-quality appliances. Both bathrooms have been tastefully updated with contemporary touches. The private backyard features a

    Jessica Brown MARK SPAIN REAL ESTATE

    3214 Lowndes Dr, Winter Park, FL 32792
  • /32

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,268 Sq Ft

    701 Denton Rd, Winter Park, FL 32792

    Seller will consider concessions. Welcome to this beautifully upgraded home in Winter Park Estates! Nestled on a quarter-acre lot, step into your private creating memories that last! This exceptional property has been meticulously maintained and enhanced with high-end features, making it a true standout. Recent upgrades include a brand-new roof (2024) and a new aluminum fence (2024), adding both

    Elizabeth Boyce CHARLES RUTENBERG REALTY ORLANDO

    701 Denton Rd, Winter Park, FL 32792
  • /23

    $539,900

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft

    426 S Lakemont Ave, Winter Park, FL 32792

    Winter Park, Outstanding Renovations! 3 BD/2 BT Pool Home! Open concept , single story with a lot of natural light. Lavish Updated Kitchen. Stainless steel appliances. Walk in the pantry. New roof 2018, New energy efficient windows and sliding glass doors, 2020, New Trane AC 2023 and New Attic ventilation fan thermostat / humidistat controlled 2024. New refrigerator. Interior includes fresh

    Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

    426 S Lakemont Ave, Winter Park, FL 32792
  • /30

    $469,000

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    1710 Aster Dr, Winter Park, FL 32792

    Price improvement!!! Renovated Winter Park home offering 3 bedrooms 2 baths with 1646 sq feet. Nice size lot .24 acre, fenced with a large open pool featuring brand new pool equipment & newly screened patio. 2024 Updates include: NEW Roof, Luxury vinyl flooring, 5 1/4 in. baseboards, popcorn ceilings removed & retextured, Full Kitchen renovation with SS appliances, Soft close cabinets & Quartz

    Dora Siler FOLIO REALTY LLC

    1710 Aster Dr, Winter Park, FL 32792
  • /36

    $1,170,000

    • 3 Beds
    • 2 Baths
    • 2,342 Sq Ft

    632 Country Club Dr, Winter Park, FL 32789

    Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this

    Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

    632 Country Club Dr, Winter Park, FL 32789
  • /36

    $1,095,000

    • 3 Beds
    • 3 Baths
    • 2,349 Sq Ft

    505 Westminster St, Orlando, FL 32803

    Exquisite, Completely Renovated Pool Home in Orwin Manor!$1,095,000 | 3 Bedrooms | 3 Full Baths | 2,349 SFDiscover the perfect marriage of timeless elegance and modern sophistication in this meticulously renovated 1947 estate, masterfully transformed by the renowned Maroon Fine Homes. This exceptional property showcases impeccable craftsmanship and thoughtful design throughout its

    Kelly Price KELLY PRICE & COMPANY LLC

    505 Westminster St, Orlando, FL 32803
  • /40

    $1,097,000

    • 3 Beds
    • 3 Baths
    • 2,460 Sq Ft

    1901 Lake Sue Dr, Orlando, FL 32803

    One story, 3-bedroom, 3 bath, RENOVATED home with resort-style backyard and screened lap pool is ready to move in to. It features a modern kitchen with a marble Breakfast bar, marble countertops and stainless-steel appliances. An Open floor plan with lots of natural light flowing throughout. The huge primary Bedroom suite with sitting area and private bath, his and hers closets, opens to the

    Pamela Stewart REALCOM REAL ESTATE SERVICES INC

    1901 Lake Sue Dr, Orlando, FL 32803
  • /61

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,960 Sq Ft

    3308 Middlesex Rd, Orlando, FL 32803

    This breathtaking Spanish-style home, winner of First Place for Design by the American Society of Interior Designers in 2020, is a true masterpiece. Designed by HGTV Designer of the Year John McClain, it blends modern luxury with timeless charm.The magazine-worthy kitchen—featured on Southern Living’s website—boasting Sherwin William's 2021 color of the year, the custom Urbane Bronze

    Julie Bettosini STOCKWORTH REALTY GROUP

    3308 Middlesex Rd, Orlando, FL 32803

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$469,190
Median Single Family Sale Price
$830,000
Median Townhouse Sale Price
$775,000
Median 2 Bedroom Sale Price
$170,000
Median 1 Bedroom Sale Price
$149,000
Average Price Per Sq Ft
$339
Number of Homes for Sale
29
Last 12 months Home Sales
171
Months of Supply
2.00
Median List Price
$630,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
5%
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